An Early Look at NBA Free Agency’s Toughest Decisions in 2019

An Early Look at NBA Free Agency’s Toughest Decisions in 2019

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    Andrew D. Bernstein/Getty Images

    More than a few teams have plenty to think about—and, ultimately, worry about—in advance of next summer’s free agency.

    Superstar flight risks. Players with undefined market values who could solicit near-max money. Marquee names who might age out of a team’s trajectory. Cornerstones recovering from injury. Mushrooming payrolls about to take a turn for the untenable.

    It’s all here. 

    Just to be clear: We’re identifying the most prominent pickles from a team’s perspective. Players who will grapple over where to sign or whether to exercise options are not included. For the most part, their decisions can wait.

    Front offices don’t have the luxury of living in the moment. They need to try to plan around every possible scenario now. And some preparations are bound to be more difficult than others.

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    Mitchell Leff/Getty Images

    Detroit Pistons: Stanley Johnson (Restricted)

    Stanley Johnson will make the Pistons’ decision a whole lot harder if he starts hitting shots outside the restricted area, preferably from deep, and finishing with more consistency in the pick-and-roll. And even if he doesn’t, they’ll still be in a bind.

    Detroit shouldn’t get into another non-shooter for big money, but it also won’t have the cap space to replace its switchiest defender.


    Miami Heat: Justise Winslow (Restricted)

    Dive deeper into salary-cap hell, or remain in regular salary-cap hell while losing a useful defender with a potentially improving jumper? 

    That’s the question the Heat face if they don’t deal Justise Winslow before next summer.


    Philadelphia 76ers: T.J. McConnell

    How much are the Sixers willing to pay a backup point guard when they have both Markelle Fultz and Ben Simmons on the docket? And when they’re trying to preserve cap space for superstar pursuits? 

    Probably less than teams who don’t have Fultz and Simmons or the money to poach A-list free agents.


    Washington Wizards: Kelly Oubre Jr. (Restricted)

    Kelly Oubre Jr. could secure a small ransom in restricted free agency if he sneaks above league-average efficiency from three and continues to hustle on defense against smaller, twitchy ball-handlers. And that, in turn, would put the Wizards in a crummy situation.

    Bankrolling salaries for Bradley Beal, Ian Mahinmi, Otto Porter and John Wall just about caps them out, and they have Markieff Morris, Austin Rivers and Tomas Satoransky all ticketed for free agency. Depending on what Dwight Howard does with his player option and how serious Washington is about keeping everyone else, Oubre’s next contract could be the difference between a hefty tax bill or avoiding one altogether. 

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    Nathaniel S. Butler/Getty Images

    The Nets are entering a simultaneously awkward and pivotal phase in their development.

    They control all of their own first-round picks, so they’re free to tank. But a few of their most important players are speeding toward significant raises, so they’ll need to render some big-picture verdicts.

    D’Angelo Russell figures to be the most expensive of the trio if his theoretical ceiling doesn’t come crashing down. Re-signing both him and Spencer Dinwiddie seems out of the question. Brooklyn can funnel only so much money into the backcourt of a non-contender. 

    Rondae Hollis-Jefferson’s next contract will be a fascinating study. He’s turned himself into a stout defender who can make some plays off the bounce, but he’s yet to parlay his mid-range game into even a semi-reliable three-point stroke. 

    Potentially grander ambitions loom over the futures of all three players. The Nets can get a crack at $60 million or more in cap space if they renounce all of their own free agents, but re-signing two of Dinwiddie, Hollis-Jefferson and Russell could displace them entirely from the max-contract discussion. 

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    Mary Schwalm/Associated Press

    The Boston Celtics’ point guard situation doesn’t come off as a legitimate hassle at first blush. Kyrie Irving is a star. They should re-sign him and then decide between keeping Terry Rozier and trading Marcus Smart.

    Poof! Problem solved. But not really.

    Irving’s own agenda could mess with Boston’s plans. He isn’t someone who seems like he’ll be swayed by open-ended title contention. He forced his way off a Cleveland Cavaliers team that still employed LeBron James and has real interest in playing with Jimmy Butler (player option), according to’s Zach Lowe. The Celtics must treat him as a flight risk even if they win a title.

    Dangling a five-year max could earn Irving’s allegiance if he’s not trying to re-explore free agency after his 10th season, in 2021, when he’s eligible for a starting salary worth 35 percent of the cap. But that deal puts serious strain on Boston’s books.

    Al Horford (player option) can hit the open market next summer as well. Gordon Hayward (player option) could be right behind in 2020. Jaylen Brown will be on his second contract by 2020-21, with Jayson Tatum following suit in 2021-22. Both may wind up being max players.

    Boston will not pay everyone. It can’t. Floating this entire core into Tatum’s next deal turns the ledger into a Golden State Warriors-Miami Heat hybrid—possibly worth it, but potentially detrimental at the same time.

    Letting Irving walk still shouldn’t be part of the Celtics’ calculus. He doesn’t turn 27 until March. Hayward and Horford are more suitable forms of collateral damage when looking at the timelines for Brown and Tatum. If nothing else, Boston should re-sign Irving, part ways with Rozier or Smart and figure out the rest later.

    It might not be that simple. Irving could get wandering eyes. He could fall off following knee surgery. He could struggle to find his offensive equilibrium as Boston integrates Hayward and props up Brown and Tatum.

    Paying Rozier would be exponentially cheaper and grant the Celtics more flexibility when looking at new contracts for the rest of the core. Picking him over Irving isn’t something any team would ever do in a vacuum, but this scenario could gain traction in Boston if Hayward recaptures previous form and Brown and Tatum remain fast-tracked toward stardom.

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    Nell Redmond/Associated Press

    Kemba Walker‘s next contract will be somebody else’s problem if the Charlotte Hornets lean into the rebuild they’re trying to stave off. But they’ve resisted beckoning fates thus far, albeit unimpressively. They could see this season through without moving him and look to continue procrastinating into 2019-20.

    Whether holding on to Walker past the February trade deadline is a mistake doesn’t matter. (It is.) Determining his price point will be an issue for every team interested in his services. 

    Although he’s not someone who should have suitors defaulting to max offers, Walker is a genuine star. Over the past three years, he’s averaged 22.8 points and 5.6 assists per 36 minutes while draining 38.6 percent of his threes—benchmarks hit by only Stephen Curry and Kyrie Irving. He’s a tad overmatched at 6’1″, but he works his tail off on defense, and Charlotte’s offense couldn’t function without him for most of last season.

    At the same time, investing anything substantial in an undersized point guard who will be one year out from his 30th birthday is tricky business.

    Including a fifth year would give the Hornets the inside track on retaining him, but what then? How much can they afford to pay Walker on a deal that takes him through his age-32 or -33 season? And does he have the window to co-headline a rebuilding project?

    Other teams will have to pore over the same questions. But the Hornets are in the most unenviable position of all.

    Pay Walker market value, and they’ve tethered their timeline to the present while adding long-term money that may not age well to an already clogged cap sheet. Let him go, though, and they’ll have forfeited a top-25 player for absolutely nothing.

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    Tony Dejak/Associated Press

    Klay Thompson’s return to the Warriors may be a formality. Kevin Durant (player option) could get the itch to leave, in which case Golden State wouldn’t be as concerned with getting trapped in the repeater’s tax for the next millennium, or Thompson could accept less to stay, as he’s already entertained doing, according to The Athletic’s Marcus Thompson.

    Bring back Durant without assurances that Splash Brother No. 2 will take a pay cut, and the process gets prickly. As’s Adrian Wojnarowski said on The Woj Pod

    “Klay Thompson…I had him on the podcast at the All-Star Weekend this past year, and he kind of said the same thing that’s he’s been very consistent on: ‘I want to be here. I don’t imagine playing anywhere else.’ I think if the Warriors are in position to be able to offer him the full max right out of the gate and not have to try to, maybe, finesse getting him to take a little bit less to fit everybody in—if he got offered the full max, I don’t know that he’d look anywhere else. If he got offered less than that, then maybe he looks.

    “But I don’t know that Klay is a guy that’s searching for something else. Some of these other guys seem to be searching for something. I don’t know that Klay fits into that. I think he loves what he has [in Golden State].”

    Penciling both Durant and Thompson in for maxes pretty much guarantees the Warriors’ payroll will shoot past $160 million. Use that figure as a baseline, and they’d be looking at a repeater tax bill in the ballpark of $105 million.

    Perhaps Warriors ownership won’t fret over this math for the first year. Their new arena, set to open in 2019-20, unlocks a new realm of revenue stream. They could be content to max out both Durant and Thompson, then re-assess their situation in 2020, when Draymond Green enters free agency.

    Everything changes if Durant doesn’t sign another short-term deal. Locking him in for the next four or five years forces the Warriors into a more imminent decision and, potentially, dissolution. Thompson could help them by signing a below-market pact, and kicking the can into 2020 will remain an option. Either way, the terms of his next contract will be a delicate matter.

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    David J. Phillip/Associated Press

    Don’t let Tobias Harris’ four-team resume fool you. The seven-year veteran is a veritable offensive hub.

    He doesn’t get to the foul line nearly enough, but he’s shored up his outside shooting and gained a better feel for spot playmaking out of the pick-and-roll. He was one of eight players last season to clear 20 points and two assists per 36 minutes while downing at least 40 percent of his threes. His company: Kevin Durant, Paul George, Kyrie Irving, Kevin Love, JJ Redick, Klay Thompson and Karl-Anthony Towns.

    It bears mentioning that Harris is the second-youngest player, behind only Towns, within this group. And the list of names to reach those benchmarks by their age-25 season over the past 10 years is similarly impressive: Durant (twice) , Irving (three times), Love, Thompson (twice), Towns, Bradley Beal, Stephen Curry (twice), Ben Gordon, Danny Granger, Blake Griffin, Kawhi Leonard and CJ McCollum (twice).

    Teams will be hot for Harris. The Los Angeles Clippers are already one of them. They offered him an $80 million deal in July that he turned down, per’s David Aldridge.

    Another suitor will give Harris more without flinching at the inclusion of a fourth year. He would just be wrapping up his age-30 season by the time said deal ends and still firmly entrenched in his prime. Even if the Clippers offer him a fifth year, they’re not on the hook for anything past his age-31 season.

    Remaining neck-and-neck with the outside market will be tough, though. Los Angeles has the means to carve out two max slots if it renounces all incumbent free agents, waives Avery Bradley ($2 million guaranteed) and orchestrates a salary dump or two. Re-signing Harris will eat up one of those spots even if he’s not earning top dollar. And he could earn top dollar from the right admirer (sup sup, Utah?).  

    Harris blurs the line between featured option and complementary weapon. Last season, he posted a 60.4 effective field-goal percentage on catch-and-shoot looks while basically matching LeBron James and Victor Oladipo’s efficiency on pull-up jumpers. According to Cleaning The Glass, the Clippers pumped in 112.8 points per 100 possessions when he played the 4, where he shouldn’t be as much of a long-term defensive liability.

    If they don’t trade him first, they’ll have to weigh the long shot of landing two stars against the prospect of paying Harris like one.

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    Phelan M. Ebenhack/Associated Press

    Keeping both Eric Bledsoe and Khris Middleton won’t be an issue for the Milwaukee Bucks if they don’t care about paying the luxury tax. Things get (a lot) more complicated should they look to duck the $132 million threshold.

    Carrying cap holds for both will run about $42 million. Whether they command that much combined cash remains to be seen, but an average of $21 million for each player feels right. Middleton might luck into more as a youngish three-and-D wing, with Bledsoe securing a smaller bag.

    Regardless, paying both could be enough to vault Milwaukee into the tax—and that’s before factoring in a sizable raise for restricted free agent Malcolm Brogdon.

    The Bucks may not care. They’ve strategically evaded the tax in each of the past two seasons. Shelling out extra cash to keep the band together is something they might be prepared to do. Expiring contracts for Matthew Dellavedova, John Henson or Tony Snell can always be moved or stretched if they’re dead set on retaining Bledsoe and Middleton without making a championship contender’s commitment.

    Choosing between the two is also an option—and an easy one at that.

    Among every player to make 50 or more appearances since 2013-14, only Middleton and Stephen Curry are averaging at least 17 points, 3.5 assists and 1.5 steals per 36 minutes while canning 39 percent of their threes. Bledsoe is a fringe All-Star in the Eastern Conference but a below-average shooter with wild-card defensive energy. Middleton plugs more holes and is the superior fit beside Giannis Antetokounmpo’s ball-dominant attack mode.

    But what happens if a cap-flush team throws near-max money at Middleton after whiffing on the primary prizes? Are the Bucks willing to pay him $25 million per year? And how high are they willing to go on Bledsoe? Can they successfully spin departures for even one of them with Antetokounmpo two years away from free agency?

    Removing the Antetokounmpo variable from the equation doesn’t make the Bucks’ job any easier. Their nucleus is approaching a put-up-or-shut-up crossroads. They won’t have the cap space to begin replacing Bledsoe or Middleton until 2020 at the earliest but cannot afford to spend themselves into oblivion for a non-contender. This season needs to unfold like a definitive tell-all or they’re going to face some mega-tough calls next summer.  

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    David Zalubowski/Associated Press

    Kristaps Porzingis will turn his next contract into a non-issue for the New York Knicks if he plays like an All-Star following his recovery from a torn left ACL. He’s a max player at full strength—a No. 1 offensive option-meets-Defensive Player of the Year candidate in the making.

    Except, the Knicks may not have a post-injury sample to work off of when Porzingis enters restricted free agency. Owner James Dolan indicated in an April interview with the New York Post‘s Larry Brooks that he’s “been told everything from December to him being out for the season” in regards to the power forward’s return. 

    Slow-playing Porzingis’ return makes sense in many respects. The Knicks won’t be competing for anything special in 2018-19. Shutting down Porzingis for the entire year bolsters the value of their draft pick and opens up extra reps for Kevin Knox, Mitchell Robinson and Noah Vonleh. It also means paying him in good faith—no small ask given Porzingis’ catalogue of injuries.

    Mirroring the 2014-15 Indiana Pacers’ approach to Paul George has some value. They let him get six games under his belt at the end of the season following a gruesome leg injury. But he wasn’t in a contract year. Six, eight, even 15 games won’t meaningfully inform the Knicks on the next four or five seasons of Porzingis’ career.

    If push comes to shove, and it probably will, New York will pay him. Another team will wager max money on an under-25 cornerstone with a superstar’s ceiling. The Knicks are risking enough if they, as expected, punt on Porzingis’ extension to plan around a more manageable cap hold for other free agents.

    Allowing him to sign elsewhere without receiving anything in return would be a nightmare scenario. They don’t have an alternative franchise face to lean on unless Knox goes boom or one of next summer’s marquee names is seduced by playing in New York.

    Acquiescing to Porzingis’ expected market poses similar risks. His four-year max is worth roughly $122.1 million. A five-year max clocks it at $158.1 million. Giving that money to anyone less than an All-NBA hopeful is a course-altering setback. And despite what Porzingis has shown to this point, the Knicks cannot mindlessly double down on his future if his 2018-19 season is severely limited by or completely lost to injury. 


    Unless otherwise noted, stats courtesy of or Basketball Reference. Salary and cap-hold information via Basketball Insiders and RealGM.

    Dan Favale covers the NBA for Bleacher Report. Follow him on Twitter (@danfavale) and listen to his Hardwood Knocks podcast, co-hosted by B/R’s Andrew Bailey.

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